EPISODE · May 6, 2026 · 6 MIN
How Michael Saylor Turned Preferred Stock Into Jet Fuel For Buying Bitcoin
from Forbes Daily Briefing · host Forbes
Last week, Strategy overtook BlackRock, issuer of the world’s largest bitcoin exchange-traded fund, IBIT, to become the world’s largest institutional holder of bitcoin. The milestone followed yet another enormous purchase: between April 13 and April 19, according to a recent Securities and Exchange Commission filing, Strategy bought $2.54 billion worth of bitcoin, its largest acquisition since November 2024. The purchase brought the company’s total holdings to 815,061 BTC—about 3.88% of bitcoin’s fixed 21 million supply—currently worth around $65 billion. The only larger holder is thought to be Satoshi Nakamoto, the elusive founder of the cryptocurrency who disappeared 15 years ago. The funding for Strategy’s latest bitcoin buying spree is not coming from flooding the market with common shares or convertible debt, but mainly from what traders affectionately call “Stretch,” a high-yield perpetual preferred stock the company has been issuing under the symbol STRC. Saylor, Strategy’s chairman, has been touting Stretch as the critical underpinning of the next phase of his bitcoin empire. From 2020 through 2024, Strategy financed its bitcoin binge largely by selling convertible notes and issuing common stock. It was a shrewd display of financial engineering while it lasted. As bitcoin climbed and investors bid Strategy shares to eye-popping premiums over the value of the company’s underlying bitcoin, Saylor could keep issuing more bonds convertible into stock and selling common shares to hedge funds and other investors anticipating a windfall. At points, the stock traded at two to three times the value of bitcoin on its balance sheet. By Nina Bambysheva, Deputy Editor Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
Last week, Strategy overtook BlackRock, issuer of the world’s largest bitcoin exchange-traded fund, IBIT, to become the world’s largest institutional holder of bitcoin. The milestone followed yet another enormous purchase: between April 13 and April 19, according to a recent Securities and Exchange Commission filing, Strategy bought $2.54 billion worth of bitcoin, its largest acquisition since November 2024. The purchase brought the company’s total holdings to 815,061 BTC—about 3.88% of bitcoin’s fixed 21 million supply—currently worth around $65 billion. The only larger holder is thought to be Satoshi Nakamoto, the elusive founder of the cryptocurrency who disappeared 15 years ago. The funding for Strategy’s latest bitcoin buying spree is not coming from flooding the market with common shares or convertible debt, but mainly from what traders affectionately call “Stretch,” a high-yield perpetual preferred stock the company has been issuing under the symbol STRC. Saylor, Strategy’s chairman, has been touting Stretch as the critical underpinning of the next phase of his bitcoin empire. From 2020 through 2024, Strategy financed its bitcoin binge largely by selling convertible notes and issuing common stock. It was a shrewd display of financial engineering while it lasted. As bitcoin climbed and investors bid Strategy shares to eye-popping premiums over the value of the company’s underlying bitcoin, Saylor could keep issuing more bonds convertible into stock and selling common shares to hedge funds and other investors anticipating a windfall. At points, the stock traded at two to three times the value of bitcoin on its balance sheet. By Nina Bambysheva, Deputy Editor Learn more about your ad choices. Visit megaphone.fm/adchoices
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How Michael Saylor Turned Preferred Stock Into Jet Fuel For Buying Bitcoin
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